diff --git a/test/images/agnhost/BASEIMAGE b/test/images/agnhost/BASEIMAGE
index 5fdb1fa08ea..cc7c45a7657 100644
--- a/test/images/agnhost/BASEIMAGE
+++ b/test/images/agnhost/BASEIMAGE
@@ -3,4 +3,6 @@ linux/arm=arm32v6/alpine:3.6
 linux/arm64=arm64v8/alpine:3.6
 linux/ppc64le=ppc64le/alpine:3.6
 linux/s390x=s390x/alpine:3.6
-windows/amd64=REGISTRY/busybox:1.29-windows-amd64
+windows/amd64/1809=REGISTRY/busybox:1.29-windows-amd64-1809
+windows/amd64/1903=REGISTRY/busybox:1.29-windows-amd64-1903
+windows/amd64/1909=REGISTRY/busybox:1.29-windows-amd64-1909
diff --git a/test/images/agnhost/README.md b/test/images/agnhost/README.md
index ce241dcd770..0b44449c231 100644
--- a/test/images/agnhost/README.md
+++ b/test/images/agnhost/README.md
@@ -639,4 +639,5 @@ The Windows `agnhost` image includes a `nc` binary that is 100% compliant with i
 ## Image
 
 The image can be found at `us.gcr.io/k8s-artifacts-prod/e2e-test-images/agnhost:2.11` for both Linux and
-Windows containers (based on `mcr.microsoft.com/windows/servercore:ltsc2019`).
+Windows containers (based on `mcr.microsoft.com/windows/servercore:ltsc2019`,
+`mcr.microsoft.com/windows/servercore:1903`, and `mcr.microsoft.com/windows/servercore:1909`).
diff --git a/test/images/busybox/BASEIMAGE b/test/images/busybox/BASEIMAGE
index 932c698c514..ce71d103b81 100644
--- a/test/images/busybox/BASEIMAGE
+++ b/test/images/busybox/BASEIMAGE
@@ -1 +1,3 @@
-windows/amd64=mcr.microsoft.com/windows/servercore:ltsc2019
+windows/amd64/1809=mcr.microsoft.com/windows/servercore:ltsc2019
+windows/amd64/1903=mcr.microsoft.com/windows/servercore:1903
+windows/amd64/1909=mcr.microsoft.com/windows/servercore:1909
diff --git a/test/images/image-util.sh b/test/images/image-util.sh
index 3917aa67a8e..20278983696 100755
--- a/test/images/image-util.sh
+++ b/test/images/image-util.sh
@@ -36,9 +36,8 @@ listOsArchs() {
 
 # Returns baseimage need to used in Dockerfile for any given architecture
 getBaseImage() {
-  os_name=$1
-  arch=$2
-  grep "${os_name}/${arch}=" BASEIMAGE | cut -d= -f2
+  os_arch=$1
+  grep "${os_arch}=" BASEIMAGE | cut -d= -f2
 }
 
 # This function will build test image for all the architectures
@@ -57,7 +56,13 @@ build() {
   kube::util::ensure-gnu-sed
 
   for os_arch in ${os_archs}; do
-    if [[ $os_arch =~ .*/.* ]]; then
+    if [[ $os_arch =~ .*/.*/.* ]]; then
+      # for Windows, we have to support both LTS and SAC channels, so we're building multiple Windows images.
+      # the format for this case is: OS/ARCH/OS_VERSION.
+      os_name=$(echo "$os_arch" | cut -d "/" -f 1)
+      arch=$(echo "$os_arch" | cut -d "/" -f 2)
+      os_version=$(echo "$os_arch" | cut -d "/" -f 3)
+    elif [[ $os_arch =~ .*/.* ]]; then
       os_name=$(echo "$os_arch" | cut -d "/" -f 1)
       arch=$(echo "$os_arch" | cut -d "/" -f 2)
     else
@@ -84,7 +89,7 @@ build() {
     TAG=$(<VERSION)
 
     if [[ -f BASEIMAGE ]]; then
-      BASEIMAGE=$(getBaseImage "${os_name}" "${arch}" | ${SED} "s|REGISTRY|${REGISTRY}|g")
+      BASEIMAGE=$(getBaseImage "${os_arch}" | ${SED} "s|REGISTRY|${REGISTRY}|g")
 
       # NOTE(claudiub): Some Windows images might require their own Dockerfile
       # while simpler ones will not. If we're building for Windows, check if
@@ -123,7 +128,7 @@ build() {
       # NOTE(claudiub): We're using a remote Windows node to build the Windows Docker images.
       # The node requires TLS authentication, and thus it is expected that the
       # ca.pem, cert.pem, key.pem files can be found in the ~/.docker folder.
-      docker --tlsverify -H "${REMOTE_DOCKER_URL}" build --pull -t "${REGISTRY}/${image}:${TAG}-${os_name}-${arch}" --build-arg BASEIMAGE="${BASEIMAGE}" -f $dockerfile_name .
+      docker --tlsverify -H "${REMOTE_DOCKER_URL}" build --isolation=hyperv --pull -t "${REGISTRY}/${image}:${TAG}-${os_name}-${arch}-${os_version}" --build-arg BASEIMAGE="${BASEIMAGE}" -f $dockerfile_name .
     else
       echo "Cannot build the image '${image}' for ${os_arch}. REMOTE_DOCKER_URL should be set, containing the URL to a Windows docker daemon."
     fi
@@ -159,7 +164,13 @@ push() {
     os_archs=$(printf 'linux/%s\n' "${!QEMUARCHS[*]}")
   fi
   for os_arch in ${os_archs}; do
-    if [[ $os_arch =~ .*/.* ]]; then
+    if [[ $os_arch =~ .*/.*/.* ]]; then
+      # for Windows, we have to support both LTS and SAC channels, so we're building multiple Windows images.
+      # the format for this case is: OS/ARCH/OS_VERSION.
+      os_name=$(echo "$os_arch" | cut -d "/" -f 1)
+      arch=$(echo "$os_arch" | cut -d "/" -f 2)
+      os_version=$(echo "$os_arch" | cut -d "/" -f 3)
+    elif [[ $os_arch =~ .*/.* ]]; then
       os_name=$(echo "$os_arch" | cut -d "/" -f 1)
       arch=$(echo "$os_arch" | cut -d "/" -f 2)
     else
@@ -171,7 +182,7 @@ push() {
       docker push "${REGISTRY}/${image}:${TAG}-${os_name}-${arch}"
     else
       # NOTE(claudiub): We're pushing the image we built on the remote Windows node.
-      docker --tlsverify -H "${REMOTE_DOCKER_URL}" push "${REGISTRY}/${image}:${TAG}-${os_name}-${arch}"
+      docker --tlsverify -H "${REMOTE_DOCKER_URL}" push "${REGISTRY}/${image}:${TAG}-${os_name}-${arch}-${os_version}"
     fi
   done
 
@@ -182,17 +193,25 @@ push() {
   # reset manifest list; needed in case multiple images are being built / pushed.
   manifest=()
   # Make os_archs list into image manifest. Eg: 'linux/amd64 linux/ppc64le' to '${REGISTRY}/${image}:${TAG}-linux-amd64 ${REGISTRY}/${image}:${TAG}-linux-ppc64le'
-  while IFS='' read -r line; do manifest+=("$line"); done < <(echo "$os_archs" | ${SED} "s~\/~-~" | ${SED} -e "s~[^ ]*~$REGISTRY\/$image:$TAG\-&~g")
+  while IFS='' read -r line; do manifest+=("$line"); done < <(echo "$os_archs" | ${SED} "s~\/~-~g" | ${SED} -e "s~[^ ]*~$REGISTRY\/$image:$TAG\-&~g")
   docker manifest create --amend "${REGISTRY}/${image}:${TAG}" "${manifest[@]}"
   for os_arch in ${os_archs}; do
-    if [[ $os_arch =~ .*/.* ]]; then
+    if [[ $os_arch =~ .*/.*/.* ]]; then
+      # for Windows, we have to support both LTS and SAC channels, so we're building multiple Windows images.
+      # the format for this case is: OS/ARCH/OS_VERSION.
       os_name=$(echo "$os_arch" | cut -d "/" -f 1)
       arch=$(echo "$os_arch" | cut -d "/" -f 2)
+      os_version=$(echo "$os_arch" | cut -d "/" -f 3)
+      suffix="$os_name-$arch-$os_version"
+    elif [[ $os_arch =~ .*/.* ]]; then
+      os_name=$(echo "$os_arch" | cut -d "/" -f 1)
+      arch=$(echo "$os_arch" | cut -d "/" -f 2)
+      suffix="$os_name-$arch"
     else
       echo "The BASEIMAGE file for the ${image} image is not properly formatted. Expected entries to start with 'os/arch', found '${os_arch}' instead."
       exit 1
     fi
-    docker manifest annotate --os "${os_name}" --arch "${arch}" "${REGISTRY}/${image}:${TAG}" "${REGISTRY}/${image}:${TAG}-${os_name}-${arch}"
+    docker manifest annotate --os "${os_name}" --arch "${arch}" "${REGISTRY}/${image}:${TAG}" "${REGISTRY}/${image}:${TAG}-${suffix}"
   done
   docker manifest push --purge "${REGISTRY}/${image}:${TAG}"
 }